Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies

Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies

Abstract We synthesized a series of novel 5-24 derivatives of oxindole. The synthesis started from 5-chlorooxindole, which was condensed with methyl 4-carboxybezoate and result in the formation of benzolyester derivatives of oxindole which was then treated with hydrazine hydrate. The oxindole benzoy...

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Published in:Bioorganic and Medicinal Chemistry Letters
Main Author: Taha M.; Ismail N.H.; Khan A.; Shah S.A.A.; Anwar A.; Halim S.A.; Fatmi M.Q.; Imran S.; Rahim F.; Khan K.M.
Format: Article
Language:English
Published: Elsevier Ltd 2015
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-84934830620&doi=10.1016%2fj.bmcl.2015.05.069&partnerID=40&md5=72aca8fc8274040351c1a7dab5aa9a93
id 2-s2.0-84934830620
spelling 2-s2.0-84934830620
Taha M.; Ismail N.H.; Khan A.; Shah S.A.A.; Anwar A.; Halim S.A.; Fatmi M.Q.; Imran S.; Rahim F.; Khan K.M.
Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
2015
Bioorganic and Medicinal Chemistry Letters
25
16
10.1016/j.bmcl.2015.05.069
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84934830620&doi=10.1016%2fj.bmcl.2015.05.069&partnerID=40&md5=72aca8fc8274040351c1a7dab5aa9a93
Abstract We synthesized a series of novel 5-24 derivatives of oxindole. The synthesis started from 5-chlorooxindole, which was condensed with methyl 4-carboxybezoate and result in the formation of benzolyester derivatives of oxindole which was then treated with hydrazine hydrate. The oxindole benzoylhydrazide was treated with aryl acetophenones and aldehydes to get target compounds 5-24. The synthesized compounds were evaluated for urease inhibition; the compound 5 (IC50 = 13.00 ± 0.35 μM) and 11 (IC50 = 19.20 ± 0.50 μM) showed potent activity as compared to the standard drug thiourea (IC50 = 21.00 ± 0.01 μM). Other compounds showed moderate to weak activity. All synthetic compounds were characterized by different spectroscopic techniques including 1H NMR, 13C NMR, IR and EI MS. The molecular interactions of the active compounds within the binding site of urease enzyme were studied through molecular docking simulations. © 2015 Elsevier Ltd.
Elsevier Ltd
0960894X
English
Article
author Taha M.; Ismail N.H.; Khan A.; Shah S.A.A.; Anwar A.; Halim S.A.; Fatmi M.Q.; Imran S.; Rahim F.; Khan K.M.
spellingShingle Taha M.; Ismail N.H.; Khan A.; Shah S.A.A.; Anwar A.; Halim S.A.; Fatmi M.Q.; Imran S.; Rahim F.; Khan K.M.
Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
author_facet Taha M.; Ismail N.H.; Khan A.; Shah S.A.A.; Anwar A.; Halim S.A.; Fatmi M.Q.; Imran S.; Rahim F.; Khan K.M.
author_sort Taha M.; Ismail N.H.; Khan A.; Shah S.A.A.; Anwar A.; Halim S.A.; Fatmi M.Q.; Imran S.; Rahim F.; Khan K.M.
title Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
title_short Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
title_full Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
title_fullStr Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
title_full_unstemmed Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
title_sort Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies
publishDate 2015
container_title Bioorganic and Medicinal Chemistry Letters
container_volume 25
container_issue 16
doi_str_mv 10.1016/j.bmcl.2015.05.069
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-84934830620&doi=10.1016%2fj.bmcl.2015.05.069&partnerID=40&md5=72aca8fc8274040351c1a7dab5aa9a93
description Abstract We synthesized a series of novel 5-24 derivatives of oxindole. The synthesis started from 5-chlorooxindole, which was condensed with methyl 4-carboxybezoate and result in the formation of benzolyester derivatives of oxindole which was then treated with hydrazine hydrate. The oxindole benzoylhydrazide was treated with aryl acetophenones and aldehydes to get target compounds 5-24. The synthesized compounds were evaluated for urease inhibition; the compound 5 (IC50 = 13.00 ± 0.35 μM) and 11 (IC50 = 19.20 ± 0.50 μM) showed potent activity as compared to the standard drug thiourea (IC50 = 21.00 ± 0.01 μM). Other compounds showed moderate to weak activity. All synthetic compounds were characterized by different spectroscopic techniques including 1H NMR, 13C NMR, IR and EI MS. The molecular interactions of the active compounds within the binding site of urease enzyme were studied through molecular docking simulations. © 2015 Elsevier Ltd.
publisher Elsevier Ltd
issn 0960894X
language English
format Article
accesstype
record_format scopus
collection Scopus
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